RO111980B1 - Fungicide composition and seeds protection method - Google Patents

Description

The present invention relates to a fungicidal composition and to a method of protecting the seeds and plants resulting from fungal diseases.

2- (4-Chloro-benzylidene} - 5 is known

5,5-dimethyl-1 - (11 + 1,2,4-triazol-1-ylmenite] -1 cyclopentanol from European Patent Application No. 89 9420520.

The compound can be obtained as follows: 2- (4-chloro-benzylidene) -5,5-dimethyl-1- (1H-1,2,4-triazole · 1-ylmethyl) -cyclopentanol (1) is prepared. ).

Structure E with more than 95%

To a mixture of 10 g of 2,2-dimethylcyclopentanone and 13.8 g of 4-clobenzaldehyde in 100 ml ethanol at 0 ° C, add 100 ml of a 25% aqueous solution of soda. After 30 min, the mixture is filtered and the solid is washed and then dried. 12.5 g of 2,2-dimethyl-5- (4-chlorobenzylidene) -1-cyclopentane [, with mp 120 ° C is obtained. . This compound dissolved in 50 ml THF is added in a solution obtained as follows:

1.9 g of sodium hydride (80% dispersion in mineral oil) are heated to 80 ° C 35 until the solid is completely dissolved in 50 ml of anhydrous DMSO. Then the solution is diluted with 100 ml THF and cooled to -10 ^c C. A solution of 11.5 g trimethylsulfonium iodide in 80 ml 40 dimethylsulfoxide is added to the mixture and the mixture is stirred for 1 5 min at -10 ° C. . An 11.8 g solution of 2,2-dimethyl-2-chloro-5 (4-chlorobenzylidene) -1-cyclopentanone is then added in 100 ml of THF. The mixture thus produced is left at ambient temperature, then poured into water and extracted with ether, washed with water, dried, distilled. 7- (4-Chlorobenzylidene) -4,4-dimethyl-1-oxaspiro- (2,4) heptane is obtained, directly usable for the next step 50.

Heat a mixture of 5 g produced with 2.8 g of 1,2,4-triazole and 11 g of potassium carbonate in 40 ml N, N-dimethylformamide for 4 h. The mixture is poured into water, extracted with ethyl acetate. The organic phase is washed, dried, recrystallized to obtain the announced product whose melting point is 143 ° C.

The structure of the product is mainly (> 95%) that in which the parachlorophenyl group is in the position E relative to the carbon bearing hydroxy group.

The method of obtaining 2,2-dimethylcyclopentanone is known in the literature

The fungicidal composition intended for propagating products according to the invention consists of (a) 2- {4-colrobenzylidene) -

5,5-dimethyl-1- (1H-1,2,4-triazol-1-ylmethyl) -1 cyclopentanol, (b) one or more fungicides suitable for the protection of the respective propagating products, an inert support in agriculture, possibly a surfactant and one or more common insecticides.

By the term "propagating product" is meant the designation of all the reproductive parts of the plant that can be used for its multiplication. We will mention, for example, the seeds of the seeds in the restricted sense), the roots, fruits, tubers, bulbs, rhizomes, parts of plants. Mention should also be made of the germinated plants and the young plants that need to be transplanted after germination or sprouting. These young plants can be protected before transplantation by total or partial treatment by immersion.

In order to choose the fungicides suitable for the protection of propagating products, the indications given in the reference works will be used and the absence of phytotoxicity of the respective products will be mentioned.

Among these works we can mention the Phytosanitary Index, 1990 edition ACT 75595 PARIS CEDEX 12.

The compositions according to the invention typically contain between one, 5 and 95% active substances.

The term "support" means an organic or mineral matter, natural or synthetic, with which

RO 111980 The active substance is associated to facilitate application on the plant, seed or soil. This support is therefore generally inert and must be acceptable for agriculture, especially on the treated plant. 5 The support may be solid (clays, natural or synthetic silicates, silica, resins, wax, solid fertilizers, etc.) or liquid (water, alcohol, ketones, petroleum fractions, aromatic or paraffinic hydrocarbons, chlorinated hydrocarbons, liquefied gases etc ...).

The surfactant can be an emulsifying, dispersing or softening agent of ionic or nonionic type. Mention may be made, for example, of salts of polyacrylic acids, salts of lignosulphonic acids, salts of phenolsulfonic or naphthalenesulphonic acids, polycondensates of ethylene oxide on fatty alcohols or on acyigrates or on fatty amines, substituted phenols (in particular 20, alkylphenols) arylphenols], salts of sulfosuccinic acids, taurine derivatives (in particular alkyldurates), phosphoric esters of polyethoxylated alcohols or phenols.

The presence of at least one surfactant is often imposed because the active matter and / or the inert carrier are not water soluble and the application vector agent is water.

The fungicidal composition according to the invention additionally contains one or more insecticides suitable for the protection of propagating products.

These include: teflutrin, cypermethrin, thiodicarb, lindane, furatiocarb, 35 acefate, butocarboxim, carbofuran, NTN, endosulfan, diethion, aldoxycarb, methocarb, oftanol (isophenphos), chlorpyrifos, bendiocarb, benfuracarb, oxam. paration, capfos, dimetoat, fonofos, chlorophenvinfos, cartap, 40 fention, fenitrotion, HCH, deltamethrin, malation, diazinon, disulfoton.

These compositions may also contain any type of ingredients such as, for example, protective colloids, adhesives, thickening agents, thixotropic agents, penetrating agents, stabilizing agents, insulating agents, pigments, dyes, polymers.

More generally, the compositions according to the invention may be associated with any solid or liquid additive corresponding to ordinary recipe techniques for applying seed treatment, in particular.

It will be borne in mind in this regard that the term "seed treatment" actually refers to the treatment of grains.

The application techniques are well known to those skilled in the art and can be used without difficulty in the present invention.

For example, filming or coating will be mentioned.

Of the compositions, solid or liquid compositions can generally be cited.

As forms of solid compositions, the powders for spraying or dispersing (with a content of compound of formula (I) can be up to 1 □□%) and the granules, in particular, those obtained by extrusion, compaction, impregnation of granulated support, the granulation starting from a powder (contained in the compound of formula (I) in these granules being between 1 and 80% for the latter).

The compositions can also be used in powder form for spraying; thus a composition containing 50 g of active material, 10 g of divided silica, 10 g of organic pigment and 970 g of talc may be used; these constituents are mixed and crushed and spray is applied.

As forms of liquid compositions or intended to constitute liquid compositions, in the case of application, solutions may be mentioned, in particular, water-soluble concentrates, emulsifiable concentrates, emulsions, concentrated suspensions, aerosols, wettable powders (or pulverizing powders), pastes , the dispersible granules.

Emulsifiable or soluble concentrates most often contain 10 to 80% of the active matter, emulsions or ready-to-use solutions containing 0.01 to 20% of the active matter.

For example, in addition to the solvent, emulsifiable concentrates may contain, where necessary, 2 to 20% suitable additives such as stabilizing agents, surfactants, penetrating agents, corrosion inhibitors, colorants or

EN 111980 Bl the above adhesives.

Starting from these concentrates, emulsions can be obtained by dissolving in water at any concentration, which are generally suitable for application to seeds. 5

The concentrated suspensions, also applicable by spraying, are prepared in such a way as to obtain a stable fluid product without deposits and usually contain 10 to 75% active material, and 0.5 to 15% surfactants, 0 , 1 to 10% thixotropic agents, O to 10% suitable additives, such as pigments, dyes, antifoams, corrosion inhibitors, stabilizing agents, penetrating agents and additives 15 and, as a carrier, water or an organic liquid in which the active matter is little or not soluble; some organic solids or mineral salts may be dissolved in the carrier to help prevent sedimentation or as antifreeze for water.

The wettable powders (or spray powders) are prepared in such a way that they contain 20 to 95% active material and typically contain in addition to 25 solid substrates, O up to 5% softening agent, 3 to 10 % dispersing agent and. when necessary, up to 10% of one or more stabilizers and / or other additives, such as pigments, 30 dyes, penetrating agents, adhesives or agents to prevent the formation of cocoons, etc.

In order to obtain these sprays or movable powders, the active materials are thoroughly mixed in suitable containers together with the additional substances and crushed into the mill or other shattering devices. Thus, spray powders are obtained whose 40 milling and suspending capacity are advantageous; they can be suspended with water at any desired concentration and these suspensions can be used very advantageously, especially for seed application. 45 Instead of wettable powders, pasta can be made. The conditions and modalities of making and using these doughs are similar to those of wettable powders or sprays. 50

The dispersible granules are usually prepared by agglomeration, in suitable granular systems, of movable powder type compositions.

Aqueous dispersions and emulsions, for example, the compositions obtained by diluting with water a wettable powder or an emulsifiable concentrate according to the invention, are within the general scope of this invention. The emulsions may be water-oil or oil-in-water and may have a consistency as thick as that of a "mayonnaise".

In the fungicidal composition according to the invention, the weight ratio of (a) 2- (4-chlorobenzylidene) -5,5-dimethyl-1 - (1H1,2,4-triazol-1-ylmethyl) -1-cyclopentanol by weight the fungicide (s) (b) is between 1/400 and 400.

On an industrial level, the propagation product is preferably a seed for cereals, corn, and rape. sunflower, soy, alfalfa, rice. A potato can be used for potatoes.

The present invention broadens the range of fungicidal compositions in that it consists of 2- (4-chlorobenzylidene) -5,5-dimethyl-1 - (1H-1,2,4-triazol-1-ylmethyl) -1 cyclopentanol, the fungicide ( a), one or more fungicides (b), with a broad spectrum in the family of derivatives of dithiocarbamic acid or dicarboxymides, a suitable support for agriculture, a surfactant and, possibly, one or more insecticides.

Fungicide (b) is selected from: captam, tyram, anti-Fusarium, thiabendazole, imidazole.benomyl, prochlorase, carbendazim, phenpiclonyl, imazalyl, anti-Rhizoctonia, fluoctolanil, mepronyl, oppression, pencicuron, tolclofos-methyl, fungicide / cete, benalaxyl, furalaxyl, oxadixyl, etridiazole, fosetyl Al, metalaxyl. himexazole, phosphoric acid or one of its calcium or potassium salts, anti-Helminthosporum fungicide, anti-cancer, coal, anti-Septoriosis, anti-Fusarium, triazoxide, fenfuran, guazatin, dodecylbenzenesulfonate of iminoctadine, amphoridium, anti-phenphorim, etpropidyl, tridemorph, 4- (3- (4-chlorophenoxyphenyl) -2methylpropyl] -2,6 dimethylmorpholine, and the ratio of fungicide (a) to fungicide (b) is between 1 400 and 400.

The method of protection of seeds against fungal diseases consists in covering the respective propagation products,

RO 111980 Bl with a fungicidal and non-phytotoxic quantity, in a proportion of 1 to 400 g with fungicide (a) and 1 to 400 g with fungicide (b) per quintal of seeds, the propagating product being a seed. 5

The compositions can be binary, ternary or quaternary in uses.

According to the first variant, fungicide (b) is a broad-spectrum fungicide chosen from ^ dithiocarbamic acid derivatives, among which we can cite (according to the name approved by the British Standard Institution or BSI or the name IUPAC):

- Iron or tris iron (dimethyldithiocarbamate), 15

- Ziram or zinc bis (dimethyldithiocarbamate),

-Nabam or disodium (dithiocarbamate)

-Zineb or zinc (dithiocarbamate) (po- 2o limer)

-Maneb or manganese ethylene bis (dithiocarbamate) (polymer),

-Mancupru, -Mancozeb or manganese complex 25 ethylene bis (dithiocarbamate), (polymer) with a zinc salt,

-Propineb or zinc propylene bis (dithiocarbamate) polymeric,

-Metam-sodium, 30

-Cuprobam,

-Tyram or tetramethylthiodysulfide, -TMTD or,

-Carbaten or, -Metiram, 35 or derivatives of dicarboximides of which we can cite:

-Captan or N- (trichloromethylthio) cyclohex-4-enene-1,2-dicarboximide,

-Folpel or N- (trichloromethylthio) fta- 4o limit,

-Capttafol or N- (1,1,2,2-tetrachloroethylthio) cyclohex-4-enene-1,2-dicarboximide, -Ditalimphos or,

-Iprione or 3- (3,5-dichlorophenyl) -N-5-isopropyl-2,4-dioxoimidazolidine-1-carboxymide,

-Procimidone or N- (3,5-dichlophenyl) 1,2-dimethylcyclopropane-1,2-dicarboximide, -Vinclozoline or (RS) -3- (3,5-dichloro-50 phenyl) -5-methyl-5- vinyl-1,3-oxazolidine-2,4-dione.

Of these derivatives, the following broad-spectrum fungicides are preferred: captan, tiram, maneb.

According to the second variant possibly taken in combination with the first variant when the fungicide (b) is a mixture, the fungicide (b) is a fungicide with anti-Fusarium activity, preferably chosen from imidazoles, of which we can cite:

-Proclorase or N-propyl- [2- (2,4,6-trichlorophenoxy) ethyl] imidazole-1-carboxamide,

-Imazalyl or allyl-1 - {2,4-dichlorophenyl] -2imidazol-1-ethylethyl ether, or carbamates may be cited:

-Benomyl or methyl 1- (butylcarbamoyl) benzimidazole-2-ylcarbamate,

-Tiabendazole or 2- (thiazol-4-yl) benzimidazole,

-Carbendazyme or methyl benzimidazole-2-ylcarbamate, or pyrroles, of which we may cite:

-Phenpiclonyl or 4- (2,3-dichlorophenyl) pyrrole-3-carbonitrile or copper oxycinoleate.

According to the third variant, taken in combination with one of the first two variants or both, when (b) it is a mixture, the fungicide (b) is with anti Rhizoctonia activity, preferably selected from dicarboximides of which we can cite :

-Iprina, or phenylureas of which we can cite:

-Pencicuron or 1- (4-chlorobenzyl) -1cyclopentyl-3-phenylureas, or anilides of which we can cite:

-Mepronil,

-Flutolanil or a, a, a-trifluoro-3'-isopropoxy-O-toluanilide, or phosphorus derivatives such as tolclofos-methyl or (3-2,6-dichloro-ptotyl 0,0-dimethylphosphonate),

According to the fourth variant, whether or not taken in combination with one or two of the first three or all three, fungicide (b) is a fungicide with antifungal activity, preferably selected from acylalanines:

-Benalaxyl or methyl N-phenylacetyl-N-

2,6-xylyl-DL-alaninate,

-Furalaxyl or methyl N- (2,6-xylyl) -DLalaninate,

-Metalaxyl or methyl N- (2-methoxyaceae)

RO 111980 With til) -N- (2,6-xylyl) -DL-alaninate,

Oxadixyl or 2-methoxy-N- {2-oxo-1,3oxazolidin-3-yl) acet-2 ', 6'-xylidide among triazoles may be cited:

-Erazrazole or ethyl 3-trichloromethyl, 2,4-thiadiazol-5-yl ether, among the isoxazoles can be cited:

-Himexazole or 5-methylisoxazole-3-ol, of the metal monoethylphosphites may be cited:

* -Fosetyl-AI or aluminum ethyl hydrogen phosphonate,

-Phosphorous acid or its alkaline (eg sodium or potassium) or alkaline earthy salts (eg calcium).

According to the fifth embodiment, whether or not taken in combination with one, two or three of the first four, fungicide (b) is a fungicide with anti-oidium activity, preferably selected from: nonphytotoxic morpholine:

-Phenpropidine or (RS) -1- [3- (4-tert-butylphenyl) -2-methylpropyl] piperidine,

-Phenpropimorph or (1] -cis-4- (3- (4-tert-butylphenyl) -2-methylpropyl] -2,6-dimethylmorpholine,

-Tridemorph or 2,6-dimethyl F4tridecylmorpholine,

-4- {3- (4Clorfenoxifenil) -2-methylpropyl) -

2,6-dimethylmorpholine, disclosed in EP-A262870; pyridines such as:

-Ethyrimol or 5-butyl-2-ethylamino-6-methylpyrimidin-4ol.

According to the sixth variant whether or not taken in combination with one or more of the first five, fungicide (b) is a fungicide with anti-Helmintosporium activity or anti-cancer, coal, antiseptoriosis, chosen from:

-Triazoxid,

-Fenfuran or 2-methyl-3-furanilide,

-Carboxy or 5-6, -dihydro-2-methyl 1,4oxatine-inine-3-carboxanilide.

-Guazatină,

- Dodecylbenzene sulphonate from iminoctadine,

-Ampropylphos or 1-aminopropic phosphonic acid.

The compositions according to the invention can be used for the protection, both preventive and curative, of the products of plant multiplication against fungi, in particular, of type Bazidiomycetes, Ascomycetes. Adelomicetesau imperfect fungi, in particular, rust, decay, oidium, cryptogamic disease of the cereals leading to their bedtime, Fisariosis, Fusarium roseum, Fusarium nivale, Helmintosporize, Rincosporioze, Septoriosis, Rizoctones of plants and plants, in general of cereals such as: wheat, barley, rye, oats and their hybrids, as well as rice and corn.

The compositions according to the invention are especially active against fungi of the Bazidiomycetes, Ascomycetes or fungus imperfections such as Botrytis cinerea, Erysiphe graminis, Puccinia graminis, Puccinia recondita, Piricularia oryzae, Cercospora beticola, Puccinia stiiformis, Fysoriumus, Erysipumarium, Erysipumarium, Erysipumarium, Erysipum oxysporum (melonis for example), Pyrenophora avenae, Septoria tritici, Septoria avenae, Whetzelinia scerotiorum, Mycosphaerella fijiensis, Alternaria solani, Aspergillus niger, Cercospora arachidicola, Cladosporium herbarium, Tilletia caries, Tilletia Rose, Fusariumum, Helusarium, Fusariumum, Heliumus teres, Helminhosporium gramineum, Helminthosporium sativum, Penicillium expansus, Pestalozzia sp, Phoma betae, Phoma foveata, Phoma lingam, Ustilago maydis, Ustilago nuda, Ustilago hordei, Ustilago avenae, Verticillium dahlinae, Asconcyata bidwell, Asconcyata bidolfi SCLE rotinia scleriticum, Sclerotinia minor, Coryneum cardinal, Rhizoctonia solani, Acrostalagmus koningi, Alternaria, Collectotnchum, Corticium rolfsii, Diplodia natalensis, Gaeumannomyces graminis, Gibberella fujikuroi, Hormodendron cladosporioides, Myrothecium vyl atra, Trichoderma pseudokoningi, Trichothecium roseum.

These compositions are used in the disinfection of cereal seeds against Ustilago nuda, Sepotoria nodorum, Tillatia caries and Tilletia controversa, Helminthosporium gramineum and many other species Fusarium sp.

As shown above, proced

RO 111980 Bl coating tiles are well known in the art and employ filming or coating techniques, for seed, or 5 for other propagation products, for immersion techniques.

The method according to the invention is applied for seed protection. Among these seeds we can mention the cereal seeds io (barley, wheat, rye, oats, wheat grains], corn, rice.

'Preferably, the seeds are covered with 1 to 4OO g fungicide (a) and 1 to 400 g fungicide (b) per 15 quintal of seeds.

However, in these intervals, non-toxic but effective fungicide doses will be chosen.

Also, when the position contains one or more insecticides, they must be applied in non-toxic doses.

The method of protection also covers the seed with 1 to 400 25 g fungicide (a) and 1 to 400 g fungicide (b) per quintal of seed.

The compositions, according to the invention, have the advantage of a wide spectrum in cereal diseases (oidium, rust, cryptogamic disease, which causes cereal bedtime, Rincosporioza, Helmintosporioosis, Septoriosis and Fusariosis), These compositions also have the advantage of their activity on the fungus 35 causes Botrytis and Cercosporids rot, and can thus be applied to propagating products of various crops such as vines, vegetable and fruit crops and tropical crops such as peanuts, bananas, coffee trees, white walnut and others.

The invention is illustrated by the examples indicated below:

Example 1. In vivo test by seed treatment:

Solution to apply:

An aqueous dispersion of the mixture of active matter with the following composition is prepared by finely milling: - active material or mixture of active matter (a) and / or (b),: 60 mg, -Tween 80 (surfactant) consisting of - a polyoxyethylene derivative oil of sorbitan diluted to a concentration of 10% in water: 0.3 mg, - it is filled up to 60 ml with water.

This aqueous dispersion is then diluted with water to obtain the desired concentration.

On Pythium arrhenomanes:

The Robbin variety grains, artificially inoculated with Pythium arrhenomane, are treated with the mixture defined above in the doses indicated in table 1.

20 grains are deposited in 10 cm 10 cm pots containing a mixture of peat: puddles (1: 1).

The small plants develop, and 15 days later, their state is compared to the control in which the colonies of Pythium arrhenomanes developed.

The results below are given for an average of 40 plants (2 pots).

Comments: In the following tables, the fungicide (a) is designated by the letter a.

Table 1

fungicides G / quintal dose "/ □ Effectiveness maneb 250 38 captan 160 97 thiram 160 100 a + thiram 100 + J60 100 a + captan 100 + 160 90 a + maneb 100 + 250 77 of 100 0

No phytotoxicity effect was found.

RO 111980 Bl

On Fusarium culmorum:

Treated barley beans, Robbin variety, naturally contaminated with Fusarium culmorum with a mixture defined above in the doses indicated in table 2 and planted as indicated in the previous test.

After 15 days of sowing, the condition of the small plants is compared to the untreated control in which colonies of Fusarium culmorum developed.

The results below are given for an average of 40 plants (2 pots).

Table 2

fungicides G / quintal dose % Efficiency thiabendazole 50 100 imazalil 5 100 benomyl 100 100 percloraz 50 100 a + tiabenzazol 25 + 50 100 a + imazalil 25 + 5 10 a + prochloraz 25 + 50 100 of 25 100

No phytotoxicity phenomenon was found.

On Rhizoctoctonia alone we:

The tests are performed in the same way as above and lead to the results shown in Table 3.

Table 3

fungicides G / quintal dose % Efficiency flutolanil two hundred 70 mepronil 500 55 iprodione 400 71 pencycuron 400 55 a + flutolanil 100 + 200 82 a + mepronil 100 + 500 73 a + iprodione 100 + 400 70 a + pencycuron 100 + 400 72 of 100 70

No phytotoxicity phenomenon was found.

On Pythium arrhenomanes:

The tests are performed under the same conditions as above and lead to the results indicated in Table 4.

RO 111980 Bl

16

Table 4

fungicides G / quintal dose % Efficiency benalaxyl 150 93 furalaxyl 150 98 etridiazole 150 98 fosetil Al 300 80 mdtalaxil 120 90 hymexazol 300 37 a + benalaxyl 100 + 150 95 a + furalaxyl 100 + 150 97 a + etridiazole 100 + 150 93 a + fossil Al 100 + 300 80 a + metalaxyl 100 + 120 93 a + hymexazol 100 + 300 32 of 100 0

No phytotoxicity phenomenon was found.

Phosphite combination (K ₂ HP0J with fungicide a:

The barley grains covered with the mixture defined above are sown in the field at a rate of 120 kg grains per hectare.

The reading is made by referring to an untreated witness at the time of germination to which the number 100 is assigned.

The biological effect is observed by counting the high plants and is expressed in table 5.

Table 5

Treatment g / q % Of plants raised from the control witness 100 Fungicide 25 + phosphite 200 126 Fungicide 25+ phosphite 40 142

After 79 days the plants are plucked from the ground and the roots of the plants are counted at an average of 20 plants

Treatment g / q Number of roots per plant witness 0.8 Fungicide 25 + phosphite 200 5.8 Fungicide 25 + phosphite 40 5.5

RO 111980 Bl

After 156 days the plants are plucked and the roots are weighed

Treatment average g / q of 20 plants Root weight per plant in mg * witness 74.7 Fungicide 25 + phosphite 200 105.5 Fungicide 25 + phosphite 40 106

* average of 20 plant tests on barley Helminthosporium

Formulations (dispersions in water) based on product (a) and iprodine or ampropylphos are made according to the preceding example. The formulations mentioned are as follows:

formulation and % of % b % C % d % e (A) (g / q) (B) (g / q) A 24 0 3.6 1.4 0.9 120 0 B 24 10 3.1 1.2 1.1 120 50 C 24 15 2.9 1.3 1.0 120 75 D 24 20 2.6 1.3 1.2 120 100 E 16 5 2.9 1.3 1.1 120 30 F 16 8 1.6 1.8 0.7 120 50 G 16 12 1.9 1.8 0.6 120 70

B, C, D: (b) = iprine

E, F, G: [b] = ampropylphos (formulations made from potassium salt) c, d, e = adjuvants c = Soprofor - Rox d = Phenophone T - 33 e = SRE

The above formulations 35 are used to combat Helminthosporium of barley. Barley seeds (Agneta variety), naturally infested by Helminthosporium gramineum and Helminthosporium terea, are therefore treated with these formulations. 4 o Each test involves 50 seeds and is repeated 4 times. The results presented, therefore, correspond to an average of 200 seeds.

These seeds are therefore planted 45 in sterile soil consisting of 60% peat,

25% sand, and 15% clay soil. They are allowed to grow 3 weeks at 5 ^C C. in the dark to encourage infestation, then at 15-17 ° C, for 2 to 3 weeks in the greenhouse to allow symptom development. The infection of the coleoptile and the leaves is controlled according to the treatment of the seeds, by visual evaluation of the percentage of the contaminated surface.

The results obtained are as follows:

RO 111980 Bl

Helminthosporium gramineum

formulation and % Efficiency % Germination witness 0 87 A 80 92 B 100 93 C 100 93 D 100 94 E 100 94 F 100 94 G 100 95

Helminthosporium teres

formulation and % Efficiency % Germination witness 0 75 A 63 88 B 97 93 C 110 91 D 100 98 E 98 94 F 100 94 G 100 96

Thus, a perfect control 3 of the mayonnaise with the compositions according to the invention is found.

Thus it is found that the association favors the branching of the roots, avoids the melting of the seeds and favors the growth of 35 cereals.

Claims (4)

claims 1. A fungicidal composition for the treatment of seeds, characterized by 4, consisting of a mixture of 2- (4-chlorobenzylidene) -5,5-dimethyl-1- (1H1,2,4-triazol-1-ylmethyl) ) -1-cyclopentanol, the fungicide (a), one or more fungicides (b), with a broad spectrum in the family of dithiocarbamic acid derivatives or dicarboximides, a suitable support for agriculture, a surfactant and possibly one or more insecticides. 2. A fungicidal composition according to claim 50, characterized in that the fungicide (b) is selected from captan, tyrant, maneb, anti-Fusarium, thiabendazole, imidazole, benomyl, procloraz, carbendazim, phenpiclonyl, imazalil, anh-Rhizoctonia, fluotolanil , mapronyl, iprodion, pencicuron, tolclofos-methyl, anti-Com / fungicide, benalaxyl, furalaxyl, oxadixyl, ethridiazole, fosetyl Al, metalaxyl, himexazole, phosphoric acid or one of its calcium or potassium salts, anti-Helmin fungicide. , anti-charcoal, anti-Septoriosis, anti-Fusarium, triazoxide, fenfuram, guazatin, iminoctadine dodecylbenzenesulfonate, ampropylphos, anti-oidium, etyrimol, phenpropidine, phenpropimorph, tridemorph, 4- [3- (4-chlorophenylphenylphenyl) -2. , 5 dimethylmorpholine. Fungicidal composition according to claim 1, characterized in that the ratio between fungicide (a) and fungicide [b] is between 1/400 and 400. 4. Method of protection of seeds against fungal diseases, characterized by the fact that they cover the products of The respective propagation with a fungicidal and nonphytotoxic amount, from a composition according to claims 1 ... 3, into a fungicide and non-phytotoxic, from a composition according to claims 1 ... 3, in a proportion of 1 to 400 g of fungicide (a) and 1 to 400 g of fungicide (b) per quintal of seed, the propagating product being a seed.